Please briefly introduce yourself and your startup.
My name is Daniel Weisman and I was the founder and CEO at Klary.
Klary at its core was TikTok for jobs — powered by collaborative filtering and natural language processing, instead of the rigid taxonomy that plagues current hiring platforms.
We wanted to develop a more modern version of LinkedIn.
The idea was, “what if we did this more like TikTok?” so people could find the job listings that look like the ones they're more interested in — and it gets smarter the more you go through.
This form of search would allow for extremely powerful look-alike targeting for both candidates and businesses.
This would create a layer of business intelligence around the relative desirability of both jobs and candidates that is sorely missing from today's hiring platforms.
While building the platform we found ourselves pushing against major data architecture constraints that resulted in major server costs and painful dev cycles due to architectural rigidity.
Because of this we started developing our own novel data architecture.
When hiring slowed in the broader market and our customers stopped hiring, we did an internal assessment and found ourselves more interested in the data architecture work that we were doing.
We decided to pivot to Jabberwocky Labs — our Notion site is here.
I had a previous startup in the InsurTech space. We did telematics based auto insurance.
We had our own completely custom underwriting. We got to market, we raised millions of dollars.
We were doing tens of millions in ARR when our strategic investor took over the company.
We did a pre-seed raise of $350k on a $5.5M cap and 10% discount SAFE to get the initial business up and running.
The timeline was rather quick because I was just coming off another start up and still had a lot of warm relationships with investors I could tap into.
Fundraising Strategy
How did you determine when to raise, how much to raise, and at what valuation?
We were just getting the idea off the ground, so we needed capital to build a backend and front end interface of a marketplace.
Our valuation was partly determined by the size of the market opportunity — LinkedIn is our main comp — and by the belief the investors had in our founding team.
What did you plan ahead of time to use the money for?
The primary goal was to build an interface that would create a reason for people to come, that would start seeding that marketplace more than anything else.
So, we scraped 2M job listings, and then we started building a little bit of a backend.
We started with traditional recruiting to start generating revenue. We had some customers as well.
But we ended up pivoting to Jabberwocky — especially after a major slow down in general market hiring that led to the loss of our largest customers.
Investor Strategy
How did you decide which investors would be a good fit?
I had warm relationships with investors from my previous company so I started with them.
Once we had to pivot the investor interest changed because we were going from a marketplace to a database business.
More generally, I think you need 2 things from an investor:
You need somebody who believes in you and your ability to execute.
They should have at least some appreciation for the space that you're in, and what you're trying to accomplish.
When you need feedback, investors who do not appreciate the space are not going to be the ones who can talk with you about the whole customer lifecycle, the journey, or the value proposition.
Fundraising Process
Roughly how many investors did you reach out to?
We had 10 meetings and 70% of our meetings led to a yes.
What did you emphasize in your pitch?
I think to a certain extent, everybody has this feeling that LinkedIn is broken. The idea of creating a more modern LinkedIn was definitely a draw.
It's a problem that almost everybody who ends up hiring touches and not even just hiring, but also self-promotion.
Given that we were raising a pre-seed round the pitch ultimately came down to the track record of the founding team.
What did you do to drive urgency among investors and close the round?
Share good news if you have it. Don't hide bad news. The more touch points you have for good news the better.
Even if they're really small wins, celebrate them, and keep investors in the loop.
What was the biggest challenge that came up during fundraising?
I can say the difference between raising for your first startup and your second or third can be night and day.
When I was raising for my first company we took over 150 meetings and only got one yes.
It was doubly difficult because we were first-time founders in a highly regulated market. Keeping the drive and passion alive through all of that rejection is very tough.
There's always risk — particularly with insurance products.
We were selling a product that is meant to make money on the margin of the premium and the float from holding the cash prior to payments.
There's going to be the potential for fraud. All of these are major risk factors that the typical startup doesn't have to think about.
Those were very much deal breakers for the vast majority of prospective investors.
Reflection
What’s one piece of fundraising advice you’d give other founders?
If you want to attract investment, you have to be able to tell stories.
For all the numbers people out there that might be a hard pill to swallow because the numbers are the story — but most people don't operate that way.
Who’s an investor you’d recommend other founders work with?
I highly recommend Eli Gordon from Hustle & Trust — specifically for Pre Seed.
I’ve known him for a long time and he’s super ethical.
He’ll be my first choice for the lead investor at Jabberwocky when we raise the pre-seed.
He’s a former founder with an exit to a publicly-traded company — he also has a strong finance background that precedes his startup days.
He’s been through the startup trenches, understands operations, and knows that things don’t always go up and to the right smoothly.
Any tools or resources you’d recommend to founders in the process of fundraising?
I like the concept of the Notion pitch deck and have integrated it into our fundraising process — like we’ve done here.
I’ve found that while most investors like to keep the first contact super condensed, others want the kitchen sink.
Having a Notion deck in addition to your regular deck allows the investors to get the kitchen sink in a really tight first-contact as well.
I also recommend a joint communication platform tool like Missive or Front.com if you and your co-founder are both fundraising.
If you’re using LinkedIn for cold outreach I like MeetAlfred.
